Detail of "39091-64-0"

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Chemical synthesis and deuterium NMR investigations of polyisoprenols: dynamics in model membranes

Chemical synthesis and deuterium NMR investigations of polyisoprenols: dynamics in model membranes. De Ropp, Jeffrey S.; Troy, Frederic A. (Sch. Med., Univ. California, Davis, CA 95616, USA). Biochemistry, 23(12), 2691-5 (English) 1984. CODEN: BICHAW. ISSN: 0006-2960. DOCUMENT TYPE: Journal CA Section: 6 (General Biochemistry) Section cross-reference(s): 22, 30 In order to investigate the ordering and motions of polyisoprenols (PIs) in membranes, a study utilizing 2H NMR of specifically 2H-labeled PIs was initiated. A synthetic route used for obtaining specifically labeled [w,w-(C2H3)2]-PIs that initiates with the selective oxidn. of the w-terminal double bond of the PI with N-bromosuccinimide is presented. Continuation of the reaction sequence produced an w-terminal aldehyde 3 C atoms shorter than the original PI. A Wittig reaction with an appropriate 2H-labeled phosphonium salt was then used to form an w-terminal-deuterated PI identical with the starting material except for replacement of 1H with 2H at the 2 w-terminal Me groups of the PI. The 2H NMR spectra of [w,w-(C2H3)2]geraniol and -farnesol incorporated into phospholipid multilamellar vesicles showed powder patterns. The quadrupole splitting of the 2H NMR signals was interpretable in terms of the degree of orderedness of the 2H-labeled site. The pure trans isomer, geraniol, gave rise to a single set of splittings for each C2H3 group, whereas farnesol, a mixt. of isomers, showed multiple quadrupole splittings. The quadrupole splittings of the PIs increased with increasing concn. of label and with lowering of temp. 58000-93-4 and 39091-64-0 which are cas registry numbers of chemicals are mentioned. 2H NMR spin-lattice relaxation (T1) measurements, revealing rates of motion of the 2H-labeled site, showed fast motion for the [w,w-(C2H3)2]geraniol relative to [w,w-(C2H3)2]cholesterol under similar conditions. A correlation time of 5 ′ 10-10 s was estd. for [w,w-(C2H3)2]geraniol, which was 1 order of magnitude faster than for [26,27-(C2H3)2]cholesterol. The synthetic scheme presented here also enabled the selective oxidn. of the w-terminal double bond of C45 solanesol to a C42 aldehyde, which will permit the synthesis of [w,w-(C2H3)2]solanesol. The synthesis of [w,w-(C2H3)2]undecaprenol and -dolichol by this reaction scheme will also be possible. In summary, these results demonstrate both the feasibility of synthesis of [w,w-(CH3)2]PIs and the utility of 2H NMR investigations of these labeled species in revealing PI order and motions in membranes. .